Question: One frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (1) Protonation

One frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (1) Protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a carboxylate ion; and (2) reaction of the carboxylate ion with CH3N2+.

(a) Draw two resonance structures of diazomethane, and account for step 1.

(b) What kind of reaction occurs in step2?

OCH3 + N2 + CH2N2 Methyl benzoate (100%) Benzoic acid Diazomethane

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